Synthesis and aldose reductase inhibitory activities of novel N-nitromethylsulfonanilide derivatives

Jun Inoue; Ying She Cui; Osamu Sakai; Yoshikuni Nakamura; Hiromi Kogiso; Peter F. Kador

doi:10.1016/S0968-0896(00)00158-9

Synthesis and aldose reductase inhibitory activities of novel N-nitromethylsulfonanilide derivatives

Jun Inoue, Ying She Cui, Osamu Sakai, Yoshikuni Nakamura, Hiromi Kogiso, Peter F. Kador

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

A novel series of 14 N-nitromethylsulfonanilide derivatives were synthesized and evaluated for their ability to inhibit recombinant aldose reductase. Computational docking simulations provided a good explanation for the observed structure-activity relationships. Kinetic analysis of (2-fluoro-5-methyl-N-methyl)-N-nitromethylsulfonanilide, 11, one of the most potent compounds in this series with an IC₅₀=0.35μM, showed uncompetitive inhibition. Subsequent in vitro culture studies of rat lenses with 11 indicated that this series of aldose reductase inhibitors are effective in either preventing or retarding sugar cataract formation associated with diabetes. Copyright (C) 2000 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	2167-2173
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	8
Issue number	8
DOIs	https://doi.org/10.1016/S0968-0896(00)00158-9
State	Published - Aug 2000
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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title = "Synthesis and aldose reductase inhibitory activities of novel N-nitromethylsulfonanilide derivatives",

abstract = "A novel series of 14 N-nitromethylsulfonanilide derivatives were synthesized and evaluated for their ability to inhibit recombinant aldose reductase. Computational docking simulations provided a good explanation for the observed structure-activity relationships. Kinetic analysis of (2-fluoro-5-methyl-N-methyl)-N-nitromethylsulfonanilide, 11, one of the most potent compounds in this series with an IC50=0.35μM, showed uncompetitive inhibition. Subsequent in vitro culture studies of rat lenses with 11 indicated that this series of aldose reductase inhibitors are effective in either preventing or retarding sugar cataract formation associated with diabetes. Copyright (C) 2000 Elsevier Science Ltd.",

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AU - Inoue, Jun

AU - Cui, Ying She

AU - Sakai, Osamu

AU - Nakamura, Yoshikuni

AU - Kogiso, Hiromi

AU - Kador, Peter F.

PY - 2000/8

Y1 - 2000/8

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AB - A novel series of 14 N-nitromethylsulfonanilide derivatives were synthesized and evaluated for their ability to inhibit recombinant aldose reductase. Computational docking simulations provided a good explanation for the observed structure-activity relationships. Kinetic analysis of (2-fluoro-5-methyl-N-methyl)-N-nitromethylsulfonanilide, 11, one of the most potent compounds in this series with an IC50=0.35μM, showed uncompetitive inhibition. Subsequent in vitro culture studies of rat lenses with 11 indicated that this series of aldose reductase inhibitors are effective in either preventing or retarding sugar cataract formation associated with diabetes. Copyright (C) 2000 Elsevier Science Ltd.

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Synthesis and aldose reductase inhibitory activities of novel N-nitromethylsulfonanilide derivatives

Abstract

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